WO2020110816A1 - Rouleau de film optique stratifié, et procédé de fabrication de celui-ci - Google Patents

Rouleau de film optique stratifié, et procédé de fabrication de celui-ci Download PDF

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Publication number
WO2020110816A1
WO2020110816A1 PCT/JP2019/045165 JP2019045165W WO2020110816A1 WO 2020110816 A1 WO2020110816 A1 WO 2020110816A1 JP 2019045165 W JP2019045165 W JP 2019045165W WO 2020110816 A1 WO2020110816 A1 WO 2020110816A1
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WIPO (PCT)
Prior art keywords
group
binder
binder layer
coating
optically anisotropic
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PCT/JP2019/045165
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English (en)
Japanese (ja)
Inventor
匡広 渥美
西川　秀幸
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富士フイルム株式会社
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Application filed by 富士フイルム株式会社 filed Critical 富士フイルム株式会社
Priority to KR1020217015449A priority Critical patent/KR102601785B1/ko
Priority to JP2020558401A priority patent/JP7138721B2/ja
Priority to CN201980078635.4A priority patent/CN113167955B/zh
Publication of WO2020110816A1 publication Critical patent/WO2020110816A1/fr

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
    • B05D1/38—Successively applying liquids or other fluent materials, e.g. without intermediate treatment with intermediate treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Definitions

  • the present invention relates to an optical laminated film roll manufacturing method and an optical laminated film roll.
  • a retardation plate made of an optically anisotropic material is used for a liquid crystal display device, an organic electroluminescence (hereinafter abbreviated as "EL") display device, a touch panel, a brightness enhancement film, and other display devices. Since these display devices have a structure in which layers having different refractive indexes are laminated, it is known that external light is reflected at the interface between the layers, which causes problems such as reduction in contrast and reflection. Therefore, these display devices (particularly, liquid crystal display devices and organic EL display devices) have conventionally been provided with a circular polarizing plate composed of a retardation plate and a polarizing film in order to suppress adverse effects due to reflection of external light. Is used.
  • Patent Document 1 describes "a liquid crystal composition containing a liquid crystal compound and a polymer which has no liquid crystallinity and produces a polar group by the action of at least one of light and acid.” [Claim 1]), and a retardation plate having at least one optically anisotropic layer formed from the liquid crystal composition, a (circular) polarizing plate, and an image display device are described ([Claim 1]). 7] to [Claim 12]).
  • Patent Document 1 describes a polymer (polarity conversion polymer) that generates a polar group contained in a liquid crystal composition, "The polarity conversion polymer contained in the liquid crystal composition is obtained by applying the liquid crystal composition onto a support.
  • Leveling function to smooth the surface when used as a retardation plate, and instead of an alignment film separately formed between optically anisotropic layers when producing a retardation plate having a plurality of optically anisotropic layers Has a function of migrating to the air interface side of the lower optically anisotropic layer to form a surface concentrated layer containing a large amount of the polarity conversion polymer. It has an alignment film function of generating a group and imparting an alignment function to the surface concentrated layer by rubbing or the like to align the liquid crystal compound to be the upper optically anisotropic layer.
  • the present inventors have confirmed that the surface concentrated layer containing a large amount of the polarity conversion polymer can be used as an alignment film as described above, but it has an alignment function. In order to achieve this, it was clarified that the surface concentrated layer had to be subjected to rubbing treatment. Therefore, the inventors of the present invention have studied the use of a novel polymer in which a photo-alignment group is further introduced into the polarity conversion polymer, and the photo-alignment treatment is applied to the surface concentrated layer to impart the alignment function (regulating force). ..
  • the present inventors have prepared an optical laminated film by forming an upper layer (optically anisotropic layer) on the surface of a lower layer (binder layer) formed using a composition containing a novel polymer.
  • an upper layer optically anisotropic layer
  • a lower layer binder layer
  • an object of the present invention is to provide an optical laminated film roll manufacturing method for producing an optical laminated film roll which is excellent in the operation of delivering an optical laminated film, and an optical laminated film roll.
  • the inventors of the present invention have conducted extensive studies to achieve the above-mentioned object, and as a result, the width of the optically anisotropic layer formed adjacent to the upper layer of the binder layer is made wider than the width of the binder layer, whereby the optical lamination
  • the present invention has been completed by finding that an optical laminated film roll excellent in film feeding operation can be produced. That is, it was found that the above-mentioned problems can be achieved by the following constitution.
  • the optically anisotropic layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound,
  • a binder layer and an optically anisotropic layer are laminated adjacent to each other, to produce a roll of an optical laminated film, a method for producing an optical laminated film roll,
  • the action step is a step in which light acts and is performed simultaneously with the binder layer forming step
  • the method for producing an optical laminated film roll according to [1] wherein the light irradiation step is a step performed between the binder layer forming step and the second coating step.
  • the optically anisotropic layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound,
  • an optical laminated film roll manufacturing method for producing an optical laminated film roll that is excellent in the operation of feeding an optical laminated film, and an optical laminated film roll.
  • a numerical range represented by “to” means a range including the numerical values before and after “to” as a lower limit value and an upper limit value.
  • the method for producing an optical laminated film roll of the present invention (hereinafter, also abbreviated as “production method of the present invention”) is a binder layer formed using a binder composition containing a binder and a photoalignable polymer.
  • a light irradiation step of irradiating polarized light or non-polarized light A second coating step of directly coating the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound on the binder layer to form a second coating film having a width wider than that of the binder layer;
  • the optical laminated film is wound into a roll, and a winding step of producing an optical laminated film.
  • the action step is a step performed between the binder layer forming step and the second coating step, or simultaneously with the binder layer forming step or the second coating step
  • the light irradiation step is the binder layer forming step. This is a step performed during the second coating step or simultaneously with the binder layer forming step or the second coating step.
  • the photo-alignable polymer has a repeating unit A containing a cleavage group which decomposes by the action of at least one selected from the group consisting of light, heat, acid and base to generate a polar group.
  • a cleavage group which has a cleavage group in the side chain and has a fluorine atom or a silicon atom on the terminal side of the side chain cleavage group, and the following condition 1 Alternatively, it is a photoalignable polymer that satisfies the condition 2.
  • Condition 1 In addition to repeating unit A, repeating unit B containing a photo-alignment group is further included.
  • Condition 2 The repeating unit A contains a photoalignable group on the main chain side of the side chain cleavage group.
  • the present invention by making the width of the optically anisotropic layer formed adjacent to the upper layer of the binder layer wider than the width of the binder layer, it is possible to obtain an optical film excellent in the operation of delivering the optical laminated film. Laminated film rolls can be made. This is not clear in detail, but the present inventors presume as follows. First, in the production method of the present invention, the air interface of the barrier layer is taken into consideration in consideration of the coating property of the composition for the optically anisotropic layer provided on the upper layer of the barrier layer (hereinafter, also referred to as “upper layer coating property”).
  • At least one selected from the group consisting of light, heat, acid and base is caused to act on the photo-alignment polymer unevenly distributed on the side to generate a polar group. Therefore, when the exposed portion of the surface of the barrier layer remains after the formation of the optically anisotropic layer, the presence of the polar group described above results in the presence of one round before when wound into a roll. It is considered that the adhesion to the back surface of the support or the like becomes easy, and as a result, the operation of delivering the optical laminated film is inferior.
  • the width of the optically anisotropic layer wider than the width of the binder layer, the surface of the binder layer having a polar group is prevented from being exposed, and as a result, it is wound into a roll. It is considered that the adhesion at the time of breaking was suppressed.
  • the first coating step, the binder layer forming step, the working step, the light irradiation step, the second coating step, the optically anisotropic layer forming step and the winding step which the manufacturing method of the present invention has, and any steps will be described. explain.
  • the first application step is a step of applying a binder composition containing a binder and a photo-alignment polymer onto a long substrate to be conveyed to form a first coating film.
  • the support examples include a polymer film that can be wound around a backup roll.
  • Materials for the polymer film include cellulose-based polymers; acrylic-based polymers having acrylic ester polymers such as polymethylmethacrylate and lactone ring-containing polymers; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyethylene terephthalate, polyethylene naphthalate, etc.
  • polyolefin polymer vinyl chloride polymer; nylon, aromatic polyamide Amide polymers such as; imide polymers; sulfone polymers; polyether sulfone polymers; polyether ether ketone polymers; polyphenylene sulfide polymers; vinylidene chloride polymers; vinyl alcohol polymers; vinyl butyral polymers; arylate polymers A polyoxymethylene-based polymer; an epoxy-based polymer; or a polymer obtained by mixing these polymers.
  • the thickness of the support is not particularly limited, but is preferably 5 to 200 ⁇ m, more preferably 10 to 100 ⁇ m, and further preferably 20 to 90 ⁇ m.
  • the binder composition to be coated on the above-mentioned support is not particularly limited as long as it is a composition containing a binder and a photo-alignable polymer described below, but contains a polymerization initiator, a photo-acid generator and a solvent. May be.
  • binder The binder contained in the binder composition is not particularly limited, and may be a resin that is simply dried and solidified (hereinafter, also referred to as “resin binder”) such that it is composed only of a resin having no polymerization reactivity. Well, it may be a polymerizable compound.
  • resin binder a resin that is simply dried and solidified
  • resin binder specifically, for example, epoxy resin, diallyl phthalate resin, silicone resin, phenol resin, unsaturated polyester resin, polyimide resin, polyurethane resin, melamine resin, urea resin, ionomer resin, ethylene ethyl acrylate resin, Acrylonitrile acrylate styrene copolymer resin, acrylonitrile styrene resin, acrylonitrile chloride polyethylene styrene copolymer resin, ethylene vinyl acetate resin, ethylene vinyl alcohol copolymer resin, acrylonitrile butadiene styrene copolymer resin, vinyl chloride resin, chlorinated polyethylene resin, polyvinylidene chloride Resin, cellulose acetate resin, fluororesin, polyoxymethylene resin, polyamide resin, polyarylate resin, thermoplastic polyurethane elastomer, polyether ether ketone resin, polyether sulfone resin
  • polymerizable compound examples include an epoxy-based monomer, an acrylic-based monomer, an oxetanyl-based monomer, and the like. Among them, the epoxy-based monomer and the acrylic-based monomer are preferable. In the present invention, a polymerizable liquid crystal compound may be used as the polymerizable compound.
  • Examples of the epoxy group-containing monomer that is an epoxy-based monomer include bisphenol A type epoxy resin, bisphenol F type epoxy resin, brominated bisphenol A type epoxy resin, bisphenol S type epoxy resin, diphenyl ether type epoxy resin, hydroquinone type epoxy resin, Naphthalene type epoxy resin, biphenyl type epoxy resin, fluorene type epoxy resin, phenol novolac type epoxy resin, orthocresol novolac type epoxy resin, trishydroxyphenylmethane type epoxy resin, trifunctional epoxy resin, tetraphenylolethane type epoxy resin, Dicyclopentadiene phenol type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol A nucleated polyol type epoxy resin, polypropylene glycol type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, glyoxal type epoxy resin, alicyclic Type epoxy resin, heterocyclic epoxy resin and the like.
  • acrylate and methacrylate monomers which are acrylic monomers
  • trifunctional monomers such as trimethylolpropane triacrylate, trimethylolpropane PO (propylene oxide) modified triacrylate, trimethylolpropane EO (ethylene oxide) modified triacrylate, and trifunctional Methylolpropane trimethacrylate and pentaerythritol triacrylate may be mentioned.
  • tetrafunctional or higher functional monomers and oligomers examples include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, and the like. be able to.
  • the polymerizable liquid crystal compound is not particularly limited, and for example, a compound capable of homeotropic alignment, homogeneous alignment, hybrid alignment and cholesteric alignment can be used.
  • liquid crystal compounds can be classified into a rod-shaped type and a disc-shaped type according to their shapes.
  • low-molecular type and high-molecular type respectively.
  • a polymer generally refers to a polymer having a degree of polymerization of 100 or more (polymer physics/phase transition dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).
  • any liquid crystal compound can be used, but a rod-shaped liquid crystal compound (hereinafter also abbreviated as “CLC”) or a discotic liquid crystal compound (discotic liquid crystal compound) (hereinafter also abbreviated as “DLC”). It is preferable to use a liquid crystal compound which is a monomer or a relatively low molecular weight compound having a degree of polymerization of less than 100.
  • Specific examples of the polymerizable group contained in the polymerizable liquid crystal compound include an acryloyl group, a methacryloyl group, an epoxy group, and a vinyl group.
  • rod-shaped liquid crystal compound for example, those described in claim 1 of JP-A-11-513019 or paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used, and are discotic.
  • liquid crystal compound for example, those described in paragraphs [0020] to [0067] of JP2007-108732A and paragraphs [0013] to [0108] of JP2010-244038A can be preferably used. However, it is not limited to these.
  • a reverse wavelength dispersion liquid crystal compound can be used as the polymerizable liquid crystal compound.
  • the “reverse wavelength dispersion” liquid crystal compound means an in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the liquid crystal compound. At that time, the Re value becomes equal or higher as the measurement wavelength becomes larger.
  • the reverse wavelength dispersive liquid crystal compound is not particularly limited as long as it can form a reverse wavelength dispersive film as described above, and is represented by, for example, the general formula (I) described in JP-A-2008-297210. (In particular, compounds described in paragraphs [0034] to [0039]) and compounds represented by the general formula (1) described in JP 2010-84032A (in particular, paragraphs [0067] to [0073] and the compounds represented by formula (1) described in JP-A-2016-081035 (particularly the compounds described in paragraphs [0043] to [0055]). be able to.
  • paragraph numbers [0028] to [0115] of WO14/147904 can be used.
  • the photo-alignable polymer contained in the binder composition (hereinafter, also referred to as the “photo-alignable polymer of the present invention” in the present specification) is at least one selected from the group consisting of light, heat, acid and base.
  • a photoalignable polymer having a repeating unit A containing a cleavage group that decomposes by the action of to produce a polar group is at least one selected from the group consisting of light, heat, acid and base.
  • the repeating unit A has a cleavage group in the side chain and has a fluorine atom or a silicon atom on the terminal side of the side chain cleavage group.
  • the photo-alignable polymer of the invention has a photo-alignable group in a mode that satisfies the following Condition 1 or Condition 2.
  • Condition 1 In addition to repeating unit A, repeating unit B containing a photo-alignment group is further included.
  • Condition 2 The repeating unit A contains a photoalignable group on the main chain side of the side chain cleavage group.
  • the “polar group” contained in the repeating unit A means a group having at least one atom of a hetero atom or a halogen atom, and specifically, for example, a hydroxyl group, a carbonyl group, a carboxy group, an amino group, a nitro group. , Ammonium group, cyano group and the like. Of these, a hydroxyl group and a carboxy group are preferable.
  • the “cleavable group that produces a polar group” refers to a group that produces the above-mentioned polar group by cleavage, but in the present invention, it also includes a group that reacts with an oxygen molecule after radical cleavage to produce a polar group.
  • the photo-alignable polymer of the invention can further suppress the film thickness unevenness of the binder layer (hereinafter, also referred to as “wind unevenness”) caused by the drying air during the drying.
  • the repeating unit A is a repeating unit represented by the following formula (1) or a repeating unit represented by the following formula (2-1) or (2-2), and the repeating unit B is a following formula (3 ) Or a repeating unit represented by the following formula (4-1) or (4-2).
  • the repeating unit A is a repeating unit represented by the following formula (1)
  • the repeating unit B is a repeating unit represented by the following formula (3).
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and in the formulas (1) and (3) R 1's may be the same or different.
  • R 1 is preferably a hydrogen atom or a methyl group.
  • X 1 and X 2 each independently represent a single bond or a divalent linking group
  • RK represents a cleavage group
  • RL represents a monovalent organic group containing a fluorine atom or a silicon atom.
  • Examples of the divalent linking group represented by X 1 and X 2 in the formulas (1), (2-1) and (2-2) include, for example, 1 to 10 carbon atoms which may have a substituent.
  • a linear, branched or cyclic alkylene group, an arylene group having 6 to 12 carbon atoms which may have a substituent, an ether group (-O-), a carbonyl group (-C( O)-) , And at least one group selected from the group consisting of an imino group (—NH—) which may have a substituent.
  • examples of the substituent that the alkylene group, the arylene group and the imino group may have include an alkyl group, an alkoxy group, a halogen atom and a hydroxyl group.
  • the alkyl group for example, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (eg, methyl group, ethyl group, propyl group, isopropyl group , N-butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.), more preferably an alkyl group having 1 to 4 carbon atoms, and a methyl group or an ethyl group.
  • alkoxy group for example, an alkoxy group having 1 to 18 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms (eg, methoxy group, ethoxy group, n-butoxy group, methoxyethoxy group, etc.) is more preferable, and carbon group It is more preferably an alkoxy group of the formula 1 to 4, and particularly preferably a methoxy group or an ethoxy group.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom and a chlorine atom are preferable.
  • linear alkylene group having 1 to 10 carbon atoms specific examples include methylene group, ethylene group, propylene group, butylene group, pentylene group, Examples thereof include a hexylene group and a decylene group.
  • branched alkylene group include a dimethylmethylene group, a methylethylene group, a 2,2-dimethylpropylene group, a 2-ethyl-2-methylpropylene group and the like.
  • cyclic alkylene group examples include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclooctylene group, a cyclodecylene group, an adamantane-diyl group and a norbornane-diyl group.
  • arylene group having 6 to 12 carbon atoms include a phenylene group, a xylylene group, a biphenylene group, a naphthylene group and a 2,2′-methylenebisphenyl group.
  • a phenylene group is particularly preferable. preferable.
  • Examples of the cleavage group represented by RK in the above formulas (1), (2-1) and (2-2) include cleavage groups represented by any of the following formulas (rk-1) to (rk-13). A group (bond) is mentioned.
  • *1 represents a bonding position with one of X 1 and X 2 in formulas (1), (2-1) and (2-2).
  • *2 represents a bonding position with the side not bonded to *1 of X 1 and X 2 in the formulas (1), (2-1) and (2-2), and
  • R represents Each independently represents a hydrogen atom or a monovalent organic group.
  • examples of the monovalent organic group represented by R include a chain or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, and the like. Can be mentioned.
  • the anion part in the above formulas (rk-10) and (rk-11) is not particularly limited because it does not affect the cleavage, and an inorganic anion or an organic anion can be used.
  • the inorganic anion include halide ions such as chloride ion and bromide ion; sulfonate anion; and the like.
  • the organic anion include carboxylate anion such as acetate anion; organic sulfonate anion such as methanesulfonate anion and paratoluenesulfonate anion; and the like.
  • the cleavage group represented by the above formula (rk-1) in the case of cleavage using light, from the viewpoint of quantum efficiency, the cleavage group represented by the above formula (rk-1) is preferable, and acid is used. In the case of the cleavage, the cleavage group represented by the above formula (rk-9) is preferable from the viewpoint of the cleavage rate.
  • Examples of the monovalent organic group containing a fluorine atom or a silicon atom represented by RL in the above formulas (1), (2-1) and (2-2) include, for example, at least one carbon atom substituted with a fluorine atom.
  • Examples of the group include an alkyl group having 1 to 20 carbon atoms and an alkenyl group having 2 to 20 carbon atoms.
  • X 1 represents a single bond or a divalent linking group
  • RO represents a photo-orienting group
  • Examples of the divalent linking group represented by X 1 in the above formulas (3), (4-1) and (4-2) include, for example, the above formulas (1), (2-1) and (2-2). The same as X 1 in the above can be mentioned.
  • the photo-alignment groups represented by RO in the above formulas (3), (4-1) and (4-2) are rearranged or changed by irradiation with light having anisotropy (for example, plane polarized light). Dimerization and isomerization due to the action of light because it is a group that has a photo-alignment function that induces an anisotropic chemical reaction and has excellent alignment uniformity and good thermal and chemical stability.
  • a photo-alignable group that produces at least one of the above is preferred.
  • the photo-orienting group that dimerizes by the action of light specifically, for example, cinnamic acid derivatives (M. Schadt et al., J. Appl. Phys., vol. 31, No. 7, page 2155 (1992)), coumarin derivatives (M. Schadt et al., Nature., vol. 381, page 212 (1996)), chalcone derivatives (Toshihiro Ogawa et al., Proceedings of Liquid Crystal Symposium, 2AB03 (1997)) , Maleimide derivatives, and groups having a skeleton of at least one derivative selected from the group consisting of benzophenone derivatives (YK Jang et al., SID Int.
  • azobenzene compound K. Ichimura et al., Mol.Cryst.Liq.Cryst ., 298,221 (1997)
  • stilbene compound JGVictor and JM Torkelson, Macromolecules, 20,2241 (1987)
  • Spiropyran compounds K. Ichimura et al., Chemistry Letters, page 1063 (1992); K. Ichimura et al., Thin Solid Films, vol. 235, page. 101 (1993)
  • cinnamic acid compound K.
  • the photo-alignment group is a group having a skeleton of at least one derivative selected from the group consisting of cinnamic acid derivatives, coumarin derivatives, chalcone derivatives and maleimide derivatives, azobenzene compounds, stilbene compounds and spiropyran compounds.
  • a group having a cinnamic acid derivative or a coumarin derivative skeleton is more preferable.
  • the repeating unit A is represented by the following formula (7) from the viewpoint of the cleavage rate and the ease of synthesis. It is a repeating unit, and the repeating unit B is preferably a repeating unit represented by the following formula (8).
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R represents a hydrogen atom or a monovalent organic group
  • a plurality of Rs may be the same. May be different.
  • X represents a hydrogen atom or a fluorine atom
  • ma and na each independently represent an integer of 1 to 20.
  • examples of the monovalent organic group represented by R include a chain or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, and the like. Can be mentioned.
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • L 1 represents a divalent linking group.
  • R 2, R 3, R 4, R 5 and R 6 each independently represent a hydrogen atom or a substituent, R 2, R 3, R 4, of R 5 and R 6, two adjacent radicals May combine with each other to form a ring.
  • R 1 in the above formula (7) is preferably a hydrogen atom or a methyl group. Further, R in the above formula (7) is preferably a hydrogen atom. Further, ma in the above formula (7) is preferably 1 or 2, and na is preferably 3 to 7. Further, X in the above formula (7) is preferably a fluorine atom.
  • repeating unit A represented by the above formula (7) examples include a repeating unit obtained by polymerizing any of the monomers represented by the following formulas (7-1) to (7-6). Can be mentioned.
  • R 1 in the above formula (8) is preferably a hydrogen atom or a methyl group.
  • the photo-alignment group is likely to interact with the liquid crystal compound, and the orientation of the optically anisotropic layer formed as the upper layer (hereinafter , Also referred to as “liquid crystal orientation”) is further improved, and a linear, branched or cyclic alkylene group having 1 to 18 carbon atoms, which may have a substituent, and a substituent are included.
  • the substituent which the alkylene group, the arylene group and the imino group may have, for example, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a cyano group, a carboxy group, an alkoxycarbonyl group. And hydroxyl groups.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom and a chlorine atom are preferable.
  • alkyl group for example, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (eg, methyl group, ethyl group, propyl group, isopropyl group , N-butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.), more preferably an alkyl group having 1 to 4 carbon atoms, and a methyl group or an ethyl group. Is particularly preferable.
  • an alkyl group having 1 to 8 carbon atoms eg, methyl group, ethyl group, propyl group, isopropyl group , N-butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.
  • an alkyl group having 1 to 4 carbon atoms
  • an alkoxy group having 1 to 18 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms (eg, methoxy group, ethoxy group, n-butoxy group, methoxyethoxy group, etc.) is more preferable, and carbon group It is more preferably an alkoxy group of the formula 1 to 4, and particularly preferably a methoxy group or an ethoxy group.
  • the aryl group include an aryl group having 6 to 12 carbon atoms, and specific examples thereof include a phenyl group, an ⁇ -methylphenyl group and a naphthyl group, and among them, a phenyl group is preferable.
  • Examples of the aryloxy group include phenoxy, naphthoxy, imidazoyloxy, benzimidazoyloxy, pyridin-4-yloxy, pyrimidinyloxy, quinazolinyloxy, purinyloxy, thiophen-3-yloxy and the like.
  • Examples of the alkoxycarbonyl group include methoxycarbonyl and ethoxycarbonyl.
  • linear alkylene group having 1 to 18 carbon atoms specific examples include methylene group, ethylene group, propylene group, butylene group, pentylene group, Examples thereof include a hexylene group, a decylene group, an undecylene group, a dodecylene group, a tridecylene group, a tetradecylene group, a pentadecylene group, a hexadecylene group, a heptadecylene group and an octadecylene group.
  • branched alkylene group examples include a dimethylmethylene group, a methylethylene group, a 2,2-dimethylpropylene group, a 2-ethyl-2-methylpropylene group and the like.
  • cyclic alkylene group examples include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclooctylene group, a cyclodecylene group, an adamantane-diyl group and a norbornane-diyl group.
  • Exo-tetrahydrodicyclopentadiene-diyl group and the like of which the cyclohexylene group is preferable.
  • arylene group having 6 to 12 carbon atoms include a phenylene group, a xylylene group, a biphenylene group, a naphthylene group and a 2,2′-methylenebisphenyl group.
  • the phenylene group is preferable. ..
  • the divalent linking group represented by L 1 in the above formula (8) is a divalent linking group containing a nitrogen atom and a cycloalkane ring, for the reason that the liquid crystal alignment is better.
  • a part of the carbon atoms constituting the cycloalkane ring may be substituted with a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur.
  • the nitrogen atom may not be present separately from the cycloalkane ring.
  • the cycloalkane ring is preferably a cycloalkane ring having 6 or more carbon atoms, and specific examples thereof include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, a cyclodocosane ring and the like.
  • L 1 in the above formula (8) is a divalent linking group represented by any of the following formulas (11) to (20) for the reason that the liquid crystal orientation is better.
  • *1 represents a bonding position with a carbon atom constituting the main chain in the above formula (8)
  • *2 represents a carbonyl group in the above formula (8). It represents the bond position with the constituent carbon atom.
  • divalent linking groups represented by any of the above formulas (11) to (20) there is a balance between the solubility in the solvent used for forming the binder layer and the solvent resistance of the binder layer obtained. From the reason of being favorable, the divalent linking group represented by any of the above formulas (12), (13), (17) and (18) is preferable.
  • R 2 , R 3 , R 4 , R 5 and R 6 in the above formula (8) may be hydrogen atoms instead of substituents.
  • the substituent represented by one embodiment of R 2 , R 3 , R 4 , R 5 and R 6 in the above formula (8) makes it easier for the photo-alignment group to interact with the liquid crystal compound and has better liquid crystal alignment. Therefore, each independently, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear halogenated alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms.
  • * represents a bonding position with the benzene ring in the above formula (8)
  • R 9 represents a monovalent organic group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom and a chlorine atom are preferable.
  • the linear alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, specifically, for example, methyl group, ethyl group. Group, n-propyl group and the like.
  • the branched alkyl group is preferably an alkyl group having 3 to 6 carbon atoms, and specific examples thereof include an isopropyl group and a tert-butyl group.
  • the cyclic alkyl group is preferably an alkyl group having 3 to 6 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.
  • the linear halogenated alkyl group having 1 to 20 carbon atoms is preferably a fluoroalkyl group having 1 to 4 carbon atoms, and specific examples thereof include a trifluoromethyl group, a perfluoroethyl group and a perfluoropropyl group. , A perfluorobutyl group, and the like, among which a trifluoromethyl group is preferable.
  • an alkoxy group having 1 to 20 carbon atoms an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 6 to 18 carbon atoms is more preferable, and an alkoxy group having 6 to 14 carbon atoms is further preferable.
  • Preferred examples thereof include groups, and among them, an n-hexyloxy group, an n-octyloxy group, an n-decyloxy group, an n-dodecyloxy group and an n-tetradecyloxy group are more preferred.
  • the aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and specific examples thereof include a phenyl group, an ⁇ -methylphenyl group and a naphthyl group. preferable.
  • the aryloxy group having 6 to 20 carbon atoms is preferably an aryloxy group having 6 to 12 carbon atoms, and specific examples thereof include a phenyloxy group and a 2-naphthyloxy group. Is preferred.
  • amino group examples include a primary amino group (—NH 2 ); a secondary amino group such as a methylamino group; a dimethylamino group, a diethylamino group, a dibenzylamino group, a nitrogen-containing heterocyclic compound (eg, pyrrolidine , Piperidine, piperazine, etc.) and a tertiary amino group such as a group having a nitrogen atom as a bond.
  • a primary amino group —NH 2
  • secondary amino group such as a methylamino group
  • a dimethylamino group a diethylamino group
  • a dibenzylamino group examples include a nitrogen-containing heterocyclic compound (eg, pyrrolidine , Piperidine, piperazine, etc.) and a tertiary amino group such as a group having a nitrogen atom as a bond.
  • a nitrogen-containing heterocyclic compound eg, pyrrolidine , Piperidine
  • examples of the monovalent organic group represented by R 9 in the above formula (10) include a linear or cyclic alkyl group having 1 to 20 carbon atoms. ..
  • the linear alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, and an n-propyl group. Among them, a methyl group or an ethyl group is preferable. preferable.
  • the cyclic alkyl group is preferably an alkyl group having a carbon number of 3 to 6, and specific examples thereof include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, and among them, a cyclohexyl group is preferable.
  • the monovalent organic group represented by R 9 in the above formula (10) may be a combination of a plurality of the above linear alkyl groups and cyclic alkyl groups directly or through a single bond. Good.
  • R 2 , R 3 , R 4 , R 5 and R in the above formula (8) are used for the reason that the photo-alignment group easily interacts with the liquid crystal compound and the liquid crystal alignment becomes better.
  • R 4 it is preferable that at least R 4 is a substituent as described above, further, improves the linearity of the resulting photoorientable copolymer tends to interact with the liquid crystal compound, liquid crystal orientation is From the reason that it is further improved, it is more preferable that R 2 , R 3 , R 5, and R 6 all represent a hydrogen atom.
  • R 4 in the above formula (8) is preferably an electron-donating substituent because the reaction efficiency is improved when the binder layer obtained is irradiated with light.
  • the electron-donating substituent refers to a substituent having a Hammett value (Hammett substituent constant ⁇ p) of 0 or less.
  • an alkyl group examples thereof include halogenated alkyl groups and alkoxy groups. Of these, an alkoxy group is preferable, and an alkoxy group having 6 to 16 carbon atoms is more preferable, because unevenness in film thickness (unevenness of wind) can be further suppressed and liquid crystal alignment becomes better. More preferably, it is an alkoxy group having 7 to 10 carbon atoms.
  • repeating unit B represented by the above formula (8) examples include a repeating unit obtained by polymerizing any of the monomers represented by the following formulas (8-1) to (8-6). Can be mentioned.
  • the photoalignable polymer of the invention may have other repeating units in addition to the repeating unit A and the repeating unit B described above.
  • Examples of such other repeating unit-forming monomers include acrylic acid ester compounds, methacrylic acid ester compounds, maleimide compounds, acrylamide compounds, acrylonitrile, maleic anhydride, styrene compounds, Examples thereof include vinyl compounds.
  • photoalignable polymer of the present invention which satisfies the condition 1 include, for example, any of the monomers represented by the above formulas (7-1) to (7-6) and the above formula (8).
  • examples thereof include copolymers using any of the monomers represented by -1) to (8-6) and any other repeating unit. Among them, the following formulas C-1 to C-5 The copolymer represented by is preferably mentioned.
  • the repeating unit A is a repeating unit represented by the following formula (5) from the viewpoint of the liquid crystal aligning property of the optically anisotropic layer formed in the upper layer. It is preferably a unit or a repeating unit represented by the following formula (6-1) or (6-2). Of these, the repeating unit A is more preferably a repeating unit represented by the following formula (5).
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and a plurality of R 1 in formula (5) may be the same or different. May be.
  • R 1 is preferably a hydrogen atom or a methyl group.
  • X 1 , X 2 and X 3 each independently represent a single bond or a divalent linking group.
  • Examples of the divalent linking group represented by X 1 , X 2 and X 3 in the formulas (5), (6-1) and (6-2) include, for example, the formulas (1) and (2 Examples thereof include those similar to X 1 in -1) and (2-2).
  • RK represents a cleavage group.
  • the cleavage group represented by RK in the above formulas (5), (6-1) and (6-2) is, for example, one of the above formulas (1), (2-1) and (2-2).
  • the cleavage group (bond) represented by any of the above formulas (rk-1) to (rk-13) can be mentioned.
  • *1 is either one of X 3 and X 2 in the formulas (5), (6-1) and (6-2).
  • R's each independently represent a hydrogen atom or a monovalent organic group.
  • RO represents a photoalignable group.
  • examples of the photo-alignment group include the same as the photo-alignment group represented by RO in the above formulas (3), (4-1) and (4-2).
  • photo-alignable polymer of the present invention which satisfies the condition 2 include polymers represented by the following formulas H-1 to H-3.
  • the weight average molecular weight (Mw) of the photoalignable polymer of the present invention is preferably from 1000 to 500000, more preferably from 1500 to 400000, particularly preferably from 2000 to 300000.
  • the number average molecular weight (Mn) of the photoalignable polymer of the present invention is preferably 500 to 250,000, more preferably 1,000 to 200,000, and particularly preferably 1500 to 150,000.
  • the dispersity (Mw/Mn) of the photoalignable polymer of the invention is preferably 1.00 to 20.00, more preferably 1.00 to 18.00, and particularly preferably 1.00 to 16.00. ..
  • the weight average molecular weight and the number average molecular weight are values measured by gel permeation chromatography (GPC) under the following conditions.
  • THF Tetrahydrofuran
  • Ecosec HLC-8220GPC manufactured by Tosoh Corporation
  • TSKgel SuperHZM-H TSKgel SuperHZ4000
  • TSKgel SuperHZM200 manufactured by Tosoh Corporation
  • Cold temperature 40°C
  • Flow rate 50 ml/min
  • the binder composition preferably contains a polymerization initiator.
  • a polymerization initiator is not particularly limited, but examples thereof include a thermal polymerization initiator and a photopolymerization initiator depending on the type of polymerization reaction.
  • a photopolymerization initiator capable of initiating a polymerization reaction by irradiation with ultraviolet rays is preferable.
  • the photopolymerization initiator for example, ⁇ -carbonyl compound (described in US Pat. Nos. 2,367,661 and 2,367,670), acyloin ether (described in US Pat. No.
  • acyloin compounds described in U.S. Pat. No. 2,722,512
  • polynuclear quinone compounds described in U.S. Pat. Nos. 3,046,127 and 2,951,758
  • combinations of triarylimidazole dimers and p-aminophenyl ketones U.S. Pat. No. 3549367
  • acridine and phenazine compounds JP-A-60-105667, US Pat. No. 4,239,850
  • oxadiazole compounds US Pat. No. 4,212,970
  • acylphosphine examples thereof include oxide compounds (described in JP-B-63-40799, JP-B-5-29234, JP-A-10-95788, and JP-A-10-29997).
  • the binder composition contains a photo-acid generator when the above-mentioned photo-alignment polymer is a polymer having a monovalent specific group containing a cleavage group which is decomposed by the action of an acid to generate a polar group.
  • a photo-acid generator when the above-mentioned photo-alignment polymer is a polymer having a monovalent specific group containing a cleavage group which is decomposed by the action of an acid to generate a polar group.
  • a photo-acid generator when the above-mentioned photo-alignment polymer is a polymer having a monovalent specific group containing a cleavage group which is decomposed by the action of an acid to generate a polar group.
  • the photo-acid generator is preferably a compound which reacts with an actinic ray having a wavelength of 300 nm or more, preferably 300 to 450 nm to generate an acid, but is not limited to its chemical structure. Further, as for a photo-acid generator which is not directly sensitive to actinic rays having a wavelength of 300 nm or more, when used in combination with a sensitizer, a compound which is sensitive to actinic rays having a wavelength of 300 nm or more and generates an acid is a It can be preferably used in combination.
  • the photoacid generator used in the present invention is preferably a photoacid generator that generates an acid with a pKa of 4 or less, more preferably a photoacid generator that generates an acid with a pKa of 3 or less, and an acid of 2 or less.
  • pKa basically refers to pKa in water at 25°C. Those that cannot be measured in water refer to those measured by changing to a solvent suitable for measurement. Specifically, pKa described in Chemical Handbook or the like can be referred to.
  • the acid having a pKa of 3 or less is preferably sulfonic acid or phosphonic acid, and more preferably sulfonic acid.
  • photoacid generators include onium salt compounds, trichloromethyl-s-triazines, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, imide sulfonate compounds, and oxime sulfonate compounds. .. Among these, onium salt compounds, imide sulfonate compounds and oxime sulfonate compounds are preferable, and onium salt compounds and oxime sulfonate compounds are particularly preferable.
  • the photoacid generator may be used alone or in combination of two or more.
  • the binder composition preferably contains a solvent from the viewpoint of workability for forming the binder layer.
  • a solvent from the viewpoint of workability for forming the binder layer.
  • the solvent include ketones (eg, acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, etc.), ethers (eg, dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, hexane).
  • Etc. alicyclic hydrocarbons (eg cyclohexane etc.), aromatic hydrocarbons (eg toluene, xylene, trimethylbenzene etc.), halogenated carbons (eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene etc.) ), esters (eg, methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (eg, ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (eg, methyl cellosolve, ethyl cellosolve, etc.), cellosolve Examples thereof include acetates, sulfoxides (eg, dimethylsulfoxide, etc.), amides (eg, dimethylformamide, dimethylacetamide, etc.), and the like, which may be used alone or in combination of two or more kinds
  • the method for applying the binder composition onto the support described above is not particularly limited, and specific examples of the application method include a spin coating method, an air knife coating method, a curtain coating method, a roller coating method, and a wire bar.
  • a coating method, a gravure coating method, a die coating method and the like can be mentioned.
  • the binder layer forming step is a step of forming a binder layer after the first coating step, and the first coating film obtained in the first coating step is subjected to a curing treatment (ultraviolet irradiation (light irradiation treatment) or It can be formed by applying a heat treatment). Moreover, although the conditions of the curing treatment are not particularly limited, it is preferable to use ultraviolet rays in the polymerization by light irradiation.
  • Irradiation amount is preferably 10mJ / cm 2 ⁇ 50J / cm 2, more preferably 20mJ / cm 2 ⁇ 5J / cm 2, more preferably 30mJ / cm 2 ⁇ 3J / cm 2 , 50 to 1000 mJ/cm 2 is particularly preferable. Further, in order to accelerate the polymerization reaction, it may be carried out under heating conditions.
  • the action step is a step of acting at least one selected from the group consisting of light, heat, acid and base.
  • the action step is between the binder layer forming step and the second coating step, or the binder layer forming step or the second coating, from the viewpoint of ensuring coating properties when forming the optically anisotropic layer as the upper layer.
  • This is a process performed at the same time as the process.
  • “between the binder layer forming step and the second applying step” means that the binder layer formed in the binder layer forming step (for example, thermal polymerization) is subjected to the action step before the second applying step. (For example, a step of applying light) is performed.
  • “simultaneously with the binder layer forming step” means a step of forming a binder layer, for example, a step of forming a binder layer by polymerization of an olefinic monomer by photoradical generation, and polymerization of an epoxy monomer by photoacid generation.
  • the action step (for example, a step of applying light) are performed at the same time. That is, it means that the light used for polymerization of the binder layer and the light used for cleavage cause two effects at the same time.
  • “simultaneously with the second coating step” means that when the second coating step is performed on the binder layer formed in the binder layer forming step (for example, photopolymerization), an action step (for example, heat is applied). Process) is performed at the same time. Among these, it is preferable from the viewpoint of process simplification that the process is performed by applying light and is performed at the same time as the binder layer forming process.
  • a method of irradiating the binder layer with ultraviolet rays can be mentioned.
  • the light source it is possible to use a lamp that emits ultraviolet rays such as a high pressure mercury lamp or a metal halide lamp.
  • the irradiation dose is preferably 10 mJ/cm 2 to 50 J/cm 2 , more preferably 20 mJ/cm 2 to 5 J/cm 2 , and more preferably 30 mJ/cm 2 to 3 J/cm 2. More preferably, it is particularly preferably 50 to 1000 mJ/cm 2 .
  • Examples of the method of applying heat include a method of heating the binder layer.
  • the heating temperature is preferably 50 to 200° C., more preferably 60 to 150° C., and particularly preferably 70 to 130° C.
  • the method of causing the acid to act for example, a method of previously adding an acid to the binder layer, a method of adding a photo-acid generator to the binder layer and generating an acid by using light as a trigger, and a binder layer
  • a method of adding a photo-acid generator to the binder layer and generating an acid by using light as a trigger, and a binder layer examples thereof include a method in which a thermal acid generator is added and heat is used as a trigger to generate an acid. Of these, the method using a photo acid generator and a thermal acid generator is preferable.
  • a method of causing the base to act for example, a method of previously adding a base to the binder layer, a method of adding a photobase generator to the binder layer and generating a base by using light as a trigger, and a binder layer
  • a method of adding a photobase generator to the binder layer and generating a base by using light as a trigger examples include a method in which a thermal base generator is added and heat is used as a trigger to generate a base.
  • the method using a photobase generator and a thermal base generator is preferable.
  • the light irradiation step is a step of irradiating polarized light or non-polarized light, that is, a step of forming a binder layer having an alignment regulating force.
  • the light irradiation step is performed between the binder layer forming step and the second coating step, or the binder layer forming step or the second step, from the viewpoint of ensuring coating properties when forming the optically anisotropic layer as the upper layer. This is a process performed at the same time as the coating process.
  • between the binder layer forming step and the second coating step means that the binder layer formed in the binder layer forming step (for example, thermal polymerization) is irradiated with the irradiation step before the second coating step. (For example, a step of irradiating polarized light) is performed.
  • “simultaneously with the binder layer forming step” means a step of forming a binder layer, for example, a step of forming a binder layer by polymerization of an olefinic monomer by photoradical generation, and polymerization of an epoxy monomer by photoacid generation.
  • the irradiation step (for example, the step of irradiating polarized light) are performed at the same time. That is, it means that the light used for polymerization of the binder layer and the light used for orientation simultaneously cause two actions.
  • “simultaneously with the second coating step” means that when the second coating step is performed on the binder layer formed in the binder layer forming step (for example, photopolymerization), the irradiation step (for example, polarized light is irradiated). Process) is performed at the same time. Among these, it is preferable that the process is performed between the binder layer forming process and the second coating process.
  • the polarized light to be irradiated is not particularly limited, and examples thereof include linearly polarized light, circularly polarized light, and elliptically polarized light, and linearly polarized light is preferable.
  • the non-polarized light to be irradiated is also called non-polarized light, and it is preferable to irradiate the coating film surface from an oblique direction.
  • the “diagonal direction” is not particularly limited as long as it is a direction inclined at a polar angle ⁇ (0 ⁇ 90°) with respect to the normal direction of the coating film surface, and can be appropriately selected according to the purpose. , ⁇ is preferably 20 to 80°.
  • a method of irradiating with light for example, a method of irradiating with polarized light of ultraviolet rays is preferably mentioned, and specifically, a method of using a polarizing plate (eg, iodine polarizing plate, dichroic dye polarizing plate, wire grid polarizing plate, etc.); Examples thereof include a method using a prism element (for example, Glan-Thompson prism, etc.) and a reflection type polarizer utilizing Brewster's angle; a method using light emitted from a laser light source having polarization.
  • a polarizing plate eg, iodine polarizing plate, dichroic dye polarizing plate, wire grid polarizing plate, etc.
  • a prism element for example, Glan-Thompson prism, etc.
  • a reflection type polarizer utilizing Brewster's angle
  • the light source used for ultraviolet irradiation is not particularly limited as long as it is a light source that emits ultraviolet light, and examples thereof include a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a carbon arc lamp, a metal halide lamp, and a xenon lamp. Can be used.
  • the second coating step is a step of directly coating the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound on the binder layer to form a second coating film having a width wider than that of the binder layer.
  • the polymerizable liquid crystal compound for example, the same compounds as those described as the binder component of the binder composition described above can be mentioned.
  • the “width of the binder layer” means the width of the binder layer formed on the support, and the width in the direction orthogonal to the transport direction of the support.
  • the method for applying the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound is not particularly limited, and examples thereof include the same method as in the first applying step.
  • the optically anisotropic layer forming step is a step of forming an optically anisotropic layer having a width wider than that of the binder layer after the second applying step to produce an optical laminated film. It can be formed by subjecting the obtained second coating film to a curing treatment (ultraviolet irradiation (light irradiation treatment) or heat treatment). Moreover, although the conditions of the curing treatment are not particularly limited, it is preferable to use ultraviolet rays in the polymerization by light irradiation.
  • Irradiation amount is preferably 10mJ / cm 2 ⁇ 50J / cm 2, more preferably 20mJ / cm 2 ⁇ 5J / cm 2, more preferably 30mJ / cm 2 ⁇ 3J / cm 2 , 50 to 1000 mJ/cm 2 is particularly preferable. Further, in order to accelerate the polymerization reaction, it may be carried out under heating conditions.
  • the winding step is a step of winding the optical laminated film into a roll after the optically anisotropic layer forming step to produce an optical laminated film roll.
  • the method of winding into a roll is not particularly limited, and examples thereof include a method of winding around a winding core by using a conveying roller.
  • the production method of the present invention may include a treatment step of performing plasma treatment or corona discharge treatment on the surface of the binder layer before the second coating step, in addition to the above-described optional operation step.
  • the plasma treatment include vacuum glow discharge and atmospheric pressure glow discharge.
  • Other methods include flame plasma treatment.
  • the corona discharge treatment is carried out by any conventionally known method, for example, Japanese Patent Publication Nos. 48-5043, 47-51905, 47-28067, 49-83767 and 51-41770. No. 51-131576, Japanese Patent Application Laid-Open No. 2001-272503, and the like.
  • the optical laminated film roll of the present invention (hereinafter, also abbreviated as “the film roll of the present invention”) is a binder layer formed by using a binder composition containing a binder and a photoalignable polymer, and on the binder layer. And an optical anisotropic layer provided on the optical anisotropic layer, the optical anisotropic layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, the binder layer and the optical anisotropic layer are adjacent to each other.
  • the optical laminated film roll is a roll-shaped product of the laminated optical laminated film, wherein the optically anisotropic layer is laminated so as to cover the surface and the end face of the binder layer.
  • the binder layer included in the film roll of the present invention is a layer formed using a binder composition containing a binder and a photoalignable polymer.
  • the method of forming the binder composition and the binder layer is the same as that described in the manufacturing method of the present invention described above.
  • the binder layer is provided as a lower layer of the optically anisotropic layer, it is in a state after the action step and the light irradiation step described in the manufacturing method of the present invention.
  • the photoalignable polymer contained in the binder layer has a homopolymer having a repeating unit containing a polar group and a photoaligning group, or a repeating unit containing a polar group and a repeating unit containing a photoalignable group. It is a copolymer.
  • the thickness of the binder layer is not particularly limited, but is preferably 0.1 to 10 ⁇ m, more preferably 0.5 to 5 ⁇ m.
  • optically anisotropic layer of the film roll of the present invention is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, as described above, and is laminated so as to cover the surface and end face of the binder layer described above.
  • a polymerizable liquid crystal composition for forming the optically anisotropic layer for example, a composition in which a polymerizable liquid crystal compound described as an optional component in the binder composition described above, a polymerization initiator and a solvent are blended. Is mentioned.
  • the method for forming the optically anisotropic layer is the same as that described in the manufacturing method of the present invention.
  • the surface and the end surface of the binder layer are intended to be the surface exposed when the polymerizable liquid crystal composition is applied, and for example, when the binder layer is formed on the support, the binder The back surface of the layer, that is, the entire front surface other than the interface with the support.
  • the thickness of the optically anisotropic layer is not particularly limited, but is preferably 0.1 to 10 ⁇ m, more preferably 0.5 to 5 ⁇ m.
  • Example 1 [Preparation of support] ⁇ Production of Cellulose Acylate Film 1> (Preparation of core layer cellulose acylate dope) The following composition was put into a mixing tank and stirred to dissolve each component, thereby preparing a cellulose acetate solution used as a core layer cellulose acylate dope.
  • Core layer Cellulose acylate dope ⁇ 100 parts by mass of cellulose acetate having a degree of acetyl substitution of 2.88 12 parts by mass of polyester compound B described in Examples of JP-A-2015-227955, 2 parts by mass of compound F below, methylene chloride (first solvent) 430 Parts by mass/methanol (second solvent) 64 parts by mass ⁇
  • the core layer cellulose acylate dope and the outer layer cellulose acylate dope are filtered through a filter paper having an average pore diameter of 34 ⁇ m and a sintered metal filter having an average pore diameter of 10 ⁇ m, and then the core layer cellulose acylate dope and outer layers arranged on both sides thereof.
  • Three layers of cellulose acylate dope were simultaneously cast on a drum at 20° C. from a casting port (band casting machine). Then, the film was peeled off in a state where the solvent content was about 20% by mass, both ends in the width direction of the film were fixed with tenter clips, and the film was dried while being stretched in the transverse direction at a draw ratio of 1.1 times. Then, the cellulose acylate film 1 having a thickness of 40 ⁇ m and a width of 1340 mm was produced by transporting between the rolls of the heat treatment apparatus.
  • the produced cellulose acylate film 1 is passed through a dielectric heating roll at a temperature of 60° C. to raise the film surface temperature to 40° C., and then an alkaline solution having the following composition is applied to one side of the film using a bar coater. An amount of 14 ml/m 2 was applied and the mixture was heated to 110°C. Then, it was conveyed for 10 seconds under a steam type far infrared heater manufactured by Noritake Co., Ltd. Next, using the same bar coater, pure water was applied at 3 ml/m 2 . Then, after washing with a fountain coater and draining with an air knife were repeated 3 times, the mixture was conveyed to a drying zone at 70° C. for 10 seconds and dried to prepare an alkali-saponified cellulose acylate film, which was used as a support.
  • Alignment Layer Y1 The alignment layer coating liquid having the following composition was continuously applied to the long saponified cellulose acetate film as described above using a #14 wire bar. After application, the coating was dried with hot air at 60° C. for 60 seconds and further with hot air at 100° C. for 120 seconds.
  • polymerization initiator (IN1) represents a photopolymerization initiator (IRGACURE2959, manufactured by BASF).
  • binder layer (liquid crystal layer)
  • the following rod-shaped liquid crystal compound A (80 parts by mass), the following rod-shaped liquid crystal compound B (20 parts by mass), a photopolymerization initiator (IRGACURE819, manufactured by BASF) (3 parts by mass), the following vertical alignment agent A (1 part by mass), The following vertical alignment agent B (0.5 parts by mass) and the following photo-alignable polymer A (3.0 parts by mass) were dissolved in 215 parts by mass of methyl ethyl ketone to prepare a binder layer (liquid crystal layer) forming solution. ..
  • the prepared binder layer forming solution was applied onto the above-mentioned alignment layer with a #3.0 wire bar to form a first coating film.
  • UV rays having a dose of 1000 mJ/cm 2 were irradiated using a 313 nm UV-LED at a surface temperature of 25° C. (UV irradiation treatment 2 ).
  • UV irradiation treatment 2 a binder layer having a film thickness of about 1 ⁇ m and a width of 1284 mm was formed.
  • the obtained binder layer was irradiated with 25 mJ/cm 2 (wavelength: 313 nm) of UV light (ultra-high pressure mercury lamp; UL750; made by HOYA) that passed through a wire grid polarizer at room temperature to impart an alignment regulating force.
  • UV light ultraviolet light (ultra-high pressure mercury lamp; UL750; made by HOYA) that passed through a wire grid polarizer at room temperature to impart an alignment regulating force.
  • the above-mentioned solution for forming an optically anisotropic layer is applied onto the binder layer having the above-mentioned orientation function by a wire bar coater #2.2 to form a second coating film having a width wider than that of the binder layer.
  • a wire bar coater #2.2 Heated at 60°C for 2 minutes and kept at 60°C while purging with nitrogen so that the oxygen concentration becomes an atmosphere of 1.0 volume% or less, an air-cooled metal halide lamp of 160 W/cm (manufactured by Eye Graphics Co., Ltd.) was used to form an optically anisotropic layer (width: 1318 mm) by irradiating an ultraviolet ray having a dose of 300 mJ/cm 2 to prepare an optical laminated film. Then, the produced optical laminated film was wound into a roll to produce an optical laminated film roll.
  • Example 2 An optical laminated film roll was produced in the same manner as in Example 1 except that the irradiation amount in the ultraviolet irradiation treatment 1 was changed to the value shown in Table 1 below and the ultraviolet irradiation treatment 2 was not performed.
  • Example 3 An optical laminated film roll was produced in the same manner as in Example 1 except that the following photo-alignment polymer B was used in place of the photo-alignment polymer A.
  • Example 4 instead of the photo-alignment polymer A, the following photo-alignment polymer C was used, and a binder layer (liquid crystal layer) forming solution was prepared by further mixing 3 parts by mass of a thermal acid generator (San-Aid SI-B3A, manufactured by Sanshin Chemical Industry Co., Ltd.). In the same manner as in Example 1, except that the heat treatment (heat treatment 2) in which the surface temperature was 120° C. was annealed for 30 seconds was applied instead of the UV irradiation treatment 2, A roll was prepared.
  • a thermal acid generator San-Aid SI-B3A, manufactured by Sanshin Chemical Industry Co., Ltd.
  • Example 5 An optical laminated film roll was produced in the same manner as in Example 1, except that the same binder layer (liquid crystal layer) forming solution as in Example 4 was used and the binder layer was formed by the following treatment. First, as shown in Table 1 below, the first coating film was dried by heating at 70° C. for 60 seconds (drying treatment). Then, as a step that also serves as an operation step, a heat treatment of annealing for 30 seconds under the condition that the surface temperature is 120° C. was performed (heat treatment 1).
  • the surface temperature is 40° C.
  • irradiation with ultraviolet rays was performed at an irradiation dose of 500 mJ/cm 2 (ultraviolet irradiation treatment 1).
  • a binder layer having a film thickness of about 1 ⁇ m was formed.
  • Example 6 An optical laminated film roll was produced in the same manner as in Example 1 except that the binder layer was formed by the following method.
  • Epoxy monomer CEL2021P; manufactured by Daicel Co., Ltd.
  • thermal acid generator San-Aid SI-B3A, manufactured by Sanshin Chemical Industry Co., Ltd.
  • the photo-alignable polymer C (2. 0 parts by mass) was dissolved in methyl ethyl ketone (300 parts by mass) to prepare a binder layer forming solution.
  • the prepared binder layer forming solution was applied onto the above-mentioned alignment layer with a #3.0 wire bar to form a first coating film.
  • Example 7 An optical laminated film was prepared in the same manner as in Example 4 except that the following photo-acid generator (B-1-1) was used in place of the thermal acid generator (San-Aid SI-B3A, manufactured by Sanshin Chemical Industry Co., Ltd.). A roll was prepared.
  • Example 8 An optical laminated film was produced in the same manner as in Example 6 except that the above photo-acid generator (B-1-1) was used in place of the thermal acid generator (San-Aid SI-B3A, manufactured by Sanshin Chemical Industry Co., Ltd.). A roll was prepared.
  • Example 9 An optical laminated film roll was produced in the same manner as in Example 7 except that the following photo-alignment polymer D was used instead of the photo-alignment polymer C.
  • Example 1 A method similar to that of Example 1 except that a second coating film having a width narrower than the width of the binder layer was formed to form the optically anisotropic layer (width: 1270 mm) when the optically anisotropic layer was formed. Then, an optical laminated film roll was produced.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Mathematical Physics (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Laminated Bodies (AREA)

Abstract

L'invention a pour objet de fournir un procédé de fabrication de rouleau de film optique stratifié selon lequel un rouleau de film optique stratifié excellent en termes de manipulation de distribution de film optique stratifié, est produit. Le procédé de fabrication de rouleau de film optique stratifié de l'invention présente : une première étape d'application au cours de laquelle une composition de liant comprenant un liant et un polymère à photo-alignement est appliquée sur un support allongé transporté, et une première membrane de revêtement est ainsi formée ; une étape de formation de couche de liant au cours de laquelle une couche de liant est formée après la première étape d'application ; une seconde étape d'application au cours de laquelle une composition de cristaux liquides polymérisable comprenant un composé de cristaux liquides polymérisable est appliquée directement sur la couche de liant, et une seconde membrane de revêtement plus large que la couche de liant est ainsi formée ; une étape de formation de couche à anisotropie optique au cours de laquelle une couche à anisotropie optique plus large que la couche de liant est formée après la seconde étape d'application, et un film optique stratifié est ainsi produit ; et une étape d'enroulement au cours de laquelle le film optique stratifié est enroulé sous forme de rouleau, et le rouleau de film optique stratifié est ainsi produit.
PCT/JP2019/045165 2018-11-28 2019-11-19 Rouleau de film optique stratifié, et procédé de fabrication de celui-ci WO2020110816A1 (fr)

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KR1020217015449A KR102601785B1 (ko) 2018-11-28 2019-11-19 광학 적층 필름롤의 제조 방법, 및 광학 적층 필름롤
JP2020558401A JP7138721B2 (ja) 2018-11-28 2019-11-19 光学積層フィルムロールの製造方法、および、光学積層フィルムロール
CN201980078635.4A CN113167955B (zh) 2018-11-28 2019-11-19 光学层叠膜辊的制造方法及光学层叠膜辊

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CN113167955B (zh) 2023-02-21
JP7138721B2 (ja) 2022-09-16

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